4-Pentylbenzoyl chloride → Methyl 3-methyl-2-(4-(4-(4-pentylbenzamido)phenyl)thiazole-2-carboxamido)butanoate

HRID 1024456Notes

Reaction equation

HRID 1024456 reaction equation
[CH2:1]([C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:15][CH:16]([CH3:39])[CH:17]([NH:22][C:23]([C:25]1[S:26][CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-])=O)=[CH:32][CH:31]=2)[N:29]=1)=[O:24])[C:18]([O:20][CH3:21])=[O:19]>>[CH3:15][CH:16]([CH3:39])[CH:17]([NH:22][C:23]([C:25]1[S:26][CH:27]=[C:28]([C:30]2[CH:35]=[CH:34][C:33]([NH:36][C:10](=[O:11])[C:9]3[CH:13]=[CH:14][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:7][CH:8]=3)=[CH:32][CH:31]=2)[N:29]=1)=[O:24])[C:18]([O:20][CH3:21])=[O:19]

Participants

3

Reactant 2

HCID 1708124-Pentylbenzoyl chlorideHCID 67150325Methyl 3-methyl-2-(4-(4-nitrophenyl)thiazole-2-carboxamido)butanoate

Product 1

HCID 52935488Methyl 3-methyl-2-(4-(4-(4-pentylbenzamido)phenyl)thiazole-2-carboxamido)butanoateYield 56%

Procedure

The title compound was synthesized analogous to Example 27, using 4-pentylbenzoyl chloride and intermediate 3. Yield: 56%; 1H NMR (DMSO-d6, 300 MHz): δ 10.32 (s, 1H), 8.84 (d, 1H), 8.37 (s, 1H), 8.12 (d, 2H), 7.91 (bs, 4H), 7.37 (d, 2H), 4.37 (t, 1H), 3.70 (s, 3H), 2.66 (s, 2H), 2.32 (m, 1H), 1.61 (s, 2H), 1.29 (s, 4H), 0.98 (t, 6H), 0.87 (s, 3H).

Sources & evidence

ORD record
ord-1aef9a743c904e85925600d306696dc3
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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